Asymmetric Hydrogenation of Furan- containing Ketones over Tartaric Acid-modified Raney Nickel Catalyst

Autores
Haruna, Noriko; Acosta, Delicia Ester; Nakagawa, Satoshi; Kohei, Yamaguchi; Akira, Tai; Okuyama, Tadashi; Takashi, Suguimura
Año de publicación
2004
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The hydrogenation of b-keto esters containing a furan unit at the conjugated position to the b-carbonyl group was carried out over a chiral heterogeneous catalyst, tartaric acid-modified Raney nickel. The hydrogenation first proceeds at the carbonyl to give optically active alcohols, but a simple substrate undergoes further hydrogenation of the furan part to produce a diastereomeric mixture of alcohols having a tetrahydrofuran moiety. This overreduction was efficiently suppressed by substitutions of a substituent at the furan part. The optical yield at the hydroxy group is in the range of 40–90%.
Fil: Haruna, Noriko. Himeji Institute Of Technology; Japón
Fil: Acosta, Delicia Ester. Himeji Institute Of Technology; Japón. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Salta. Instituto de Investigaciones para la Industria Química. Universidad Nacional de Salta. Facultad de Ingeniería. Instituto de Investigaciones para la Industria Química; Argentina
Fil: Nakagawa, Satoshi. Himeji Institute Of Technology; Japón
Fil: Kohei, Yamaguchi. Himeji Institute Of Technology; Japón
Fil: Akira, Tai. Himeji Institute Of Technology; Japón
Fil: Okuyama, Tadashi. Himeji Institute Of Technology; Japón
Fil: Takashi, Suguimura. Himeji Institute Of Technology; Japón
Materia
Asymetric Hydrogenation
Furane
Tartaric Modified Raney Nickel
Ketones
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/76786
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Asymmetric Hydrogenation of Furan- containing Ketones over Tartaric Acid-modified Raney Nickel CatalystHaruna, NorikoAcosta, Delicia EsterNakagawa, SatoshiKohei, YamaguchiAkira, TaiOkuyama, TadashiTakashi, SuguimuraAsymetric HydrogenationFuraneTartaric Modified Raney NickelKetoneshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The hydrogenation of b-keto esters containing a furan unit at the conjugated position to the b-carbonyl group was carried out over a chiral heterogeneous catalyst, tartaric acid-modified Raney nickel. The hydrogenation first proceeds at the carbonyl to give optically active alcohols, but a simple substrate undergoes further hydrogenation of the furan part to produce a diastereomeric mixture of alcohols having a tetrahydrofuran moiety. This overreduction was efficiently suppressed by substitutions of a substituent at the furan part. The optical yield at the hydroxy group is in the range of 40–90%.Fil: Haruna, Noriko. Himeji Institute Of Technology; JapónFil: Acosta, Delicia Ester. Himeji Institute Of Technology; Japón. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Salta. Instituto de Investigaciones para la Industria Química. Universidad Nacional de Salta. Facultad de Ingeniería. Instituto de Investigaciones para la Industria Química; ArgentinaFil: Nakagawa, Satoshi. Himeji Institute Of Technology; JapónFil: Kohei, Yamaguchi. Himeji Institute Of Technology; JapónFil: Akira, Tai. Himeji Institute Of Technology; JapónFil: Okuyama, Tadashi. Himeji Institute Of Technology; JapónFil: Takashi, Suguimura. Himeji Institute Of Technology; JapónPergamon-Elsevier Science Ltd2004-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/76786Haruna, Noriko; Acosta, Delicia Ester; Nakagawa, Satoshi; Kohei, Yamaguchi; Akira, Tai; et al.; Asymmetric Hydrogenation of Furan- containing Ketones over Tartaric Acid-modified Raney Nickel Catalyst; Pergamon-Elsevier Science Ltd; Heterocycles; 62; 1; 12-2004; 375-3861881-0942CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.3987/COM-03-S(P)17info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:49:02Zoai:ri.conicet.gov.ar:11336/76786instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 09:49:02.469CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Asymmetric Hydrogenation of Furan- containing Ketones over Tartaric Acid-modified Raney Nickel Catalyst
title Asymmetric Hydrogenation of Furan- containing Ketones over Tartaric Acid-modified Raney Nickel Catalyst
spellingShingle Asymmetric Hydrogenation of Furan- containing Ketones over Tartaric Acid-modified Raney Nickel Catalyst
Haruna, Noriko
Asymetric Hydrogenation
Furane
Tartaric Modified Raney Nickel
Ketones
title_short Asymmetric Hydrogenation of Furan- containing Ketones over Tartaric Acid-modified Raney Nickel Catalyst
title_full Asymmetric Hydrogenation of Furan- containing Ketones over Tartaric Acid-modified Raney Nickel Catalyst
title_fullStr Asymmetric Hydrogenation of Furan- containing Ketones over Tartaric Acid-modified Raney Nickel Catalyst
title_full_unstemmed Asymmetric Hydrogenation of Furan- containing Ketones over Tartaric Acid-modified Raney Nickel Catalyst
title_sort Asymmetric Hydrogenation of Furan- containing Ketones over Tartaric Acid-modified Raney Nickel Catalyst
dc.creator.none.fl_str_mv Haruna, Noriko
Acosta, Delicia Ester
Nakagawa, Satoshi
Kohei, Yamaguchi
Akira, Tai
Okuyama, Tadashi
Takashi, Suguimura
author Haruna, Noriko
author_facet Haruna, Noriko
Acosta, Delicia Ester
Nakagawa, Satoshi
Kohei, Yamaguchi
Akira, Tai
Okuyama, Tadashi
Takashi, Suguimura
author_role author
author2 Acosta, Delicia Ester
Nakagawa, Satoshi
Kohei, Yamaguchi
Akira, Tai
Okuyama, Tadashi
Takashi, Suguimura
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Asymetric Hydrogenation
Furane
Tartaric Modified Raney Nickel
Ketones
topic Asymetric Hydrogenation
Furane
Tartaric Modified Raney Nickel
Ketones
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The hydrogenation of b-keto esters containing a furan unit at the conjugated position to the b-carbonyl group was carried out over a chiral heterogeneous catalyst, tartaric acid-modified Raney nickel. The hydrogenation first proceeds at the carbonyl to give optically active alcohols, but a simple substrate undergoes further hydrogenation of the furan part to produce a diastereomeric mixture of alcohols having a tetrahydrofuran moiety. This overreduction was efficiently suppressed by substitutions of a substituent at the furan part. The optical yield at the hydroxy group is in the range of 40–90%.
Fil: Haruna, Noriko. Himeji Institute Of Technology; Japón
Fil: Acosta, Delicia Ester. Himeji Institute Of Technology; Japón. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Salta. Instituto de Investigaciones para la Industria Química. Universidad Nacional de Salta. Facultad de Ingeniería. Instituto de Investigaciones para la Industria Química; Argentina
Fil: Nakagawa, Satoshi. Himeji Institute Of Technology; Japón
Fil: Kohei, Yamaguchi. Himeji Institute Of Technology; Japón
Fil: Akira, Tai. Himeji Institute Of Technology; Japón
Fil: Okuyama, Tadashi. Himeji Institute Of Technology; Japón
Fil: Takashi, Suguimura. Himeji Institute Of Technology; Japón
description The hydrogenation of b-keto esters containing a furan unit at the conjugated position to the b-carbonyl group was carried out over a chiral heterogeneous catalyst, tartaric acid-modified Raney nickel. The hydrogenation first proceeds at the carbonyl to give optically active alcohols, but a simple substrate undergoes further hydrogenation of the furan part to produce a diastereomeric mixture of alcohols having a tetrahydrofuran moiety. This overreduction was efficiently suppressed by substitutions of a substituent at the furan part. The optical yield at the hydroxy group is in the range of 40–90%.
publishDate 2004
dc.date.none.fl_str_mv 2004-12
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/76786
Haruna, Noriko; Acosta, Delicia Ester; Nakagawa, Satoshi; Kohei, Yamaguchi; Akira, Tai; et al.; Asymmetric Hydrogenation of Furan- containing Ketones over Tartaric Acid-modified Raney Nickel Catalyst; Pergamon-Elsevier Science Ltd; Heterocycles; 62; 1; 12-2004; 375-386
1881-0942
CONICET Digital
CONICET
url http://hdl.handle.net/11336/76786
identifier_str_mv Haruna, Noriko; Acosta, Delicia Ester; Nakagawa, Satoshi; Kohei, Yamaguchi; Akira, Tai; et al.; Asymmetric Hydrogenation of Furan- containing Ketones over Tartaric Acid-modified Raney Nickel Catalyst; Pergamon-Elsevier Science Ltd; Heterocycles; 62; 1; 12-2004; 375-386
1881-0942
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.3987/COM-03-S(P)17
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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